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How to Choose Your Next Destination

May 5, 2025

Both Croatia & Greece have started to open borders to travelers that are vaccinated or test negative for COVID-19. This means the time to book the Mediterranian is now. From tantalizing cuisine to secluded beaches,

Destined can help put together a

well-rounded vacation you are looking for. We've put together some of our most popular options below.

The Best Deals this Summer

May 5, 2021

Chapter Credit: Scott's Cheap Flights new book: Take More Vacations

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Let’s say you work in an office that gives you three weeks of vacation per year. How should you split up that time to generate the most happiness?

One school of thought is to use all your time off on a single big, long trip. Spend three weeks meandering around South America or Southeast Asia because an extended amount of time is the best way to get to know a place.

Advocates of “slow travel” will point to a few justifications. First, it’s expensive to fly overseas, so taking one long trip means purchasing only one roundtrip flight. Second, it’s lengthy and exhausting to fly internationally, not to mention jet lag. If you’re going to fly all that way, a longer trip maximizes the ratio of time on the ground to time in transit. Third, a long trip is the best way to relax and experience a place beyond just surface level.

Let’s examine these ideas individually. First, while expensive flights are certainly prevalent, we’ll explore in Chapter 3 why they’re a choice, not a requirement. We are living in the Golden Age of Cheap Flights; it’s never been less expensive to travel overseas than it is today. Even a decade ago, flights to Europe under $1,000 roundtrip were rare, but now they’re regularly available under $400 roundtrip. Like a form of travel inflation, taking three trips abroad in 2021 is akin to taking one overseas trip in 2011.

The second idea of maximizing vacation time to transit time is the most defensible. Nobody would argue that flying to Thailand for a one-day vacation is a good use of time, after all. However, what’s harder to defend is the notion that people should wait 49 weeks between vacations. Once a relaxing three-week vacation has ended, it’s a long, vacation-less slog waiting for your next trip.

What about the argument that traveling slowly is the best way to relax and absorb your surroundings? For many people it is. But slow travel isn’t a free lunch. For people who have a limited amount of vacation time, slow travel means fewer trips. It’s putting all your eggs in one basket. If you’ve got three weeks of vacation and you use it all on a trip to Fiji, what happens if by Day 3 you decide you don’t much like Fiji? You may wish you had tested it with a shorter trip first. Like investment portfolios, there’s value in diversifying your travels.

Even the very notion that longer vacations are more relaxing is worth questioning. In 2013, Dutch researchers at Radboud University in Nijmegen published a study examining trip length and vacationers’ health and well-being.

They surveyed travelers on longer vacations, 23 days on average, and found that well-being peaked on Day 8 and declined thereafter. There was no afterglow effect on individuals following a trip, as their health and wellness ratings reverted to pre-vacation levels within a week of return. “Frequent respites might be more important to preserve well-being than the duration of one single [vacation],” the authors concluded. Three one-week vacations may do us more good than one three-week vacation. Vacations, like many parts of life, have diminishing marginal utility.

Taking one vacation a year elevates the importance of that trip. I mean, if it’s your one chance to go somewhere, the stakes are high. So where do you go? Traditional tourist favorites, the big hits: Paris, Tokyo, Sydney, London. They may be crowded and expensive, but with one trip per year, you can’t risk going somewhere off the beaten path. What if it sucks?

[Author’s note: In the book, I give the examples of Priya and Tom. Tom uses all his vacation time on one trip, while Priya divides hers into three.]

If instead you follow Priya’s lead and aim for three trips a year instead of one, you can visit places further down your list, or ones you’d never even considered. With multiple trips, any one risk is less risky, and the payout is potentially much larger. By testing out different destinations, you can figure out which places jibe with you personally, rather than which places are most likely to jibe with the average tourist. You can take a risk on Latvia or Togo or Laos, places that aren’t widely popular but are adored by some. Best case: You find a hidden gem and fall in love, like Priya did with Guatemala. Worst case: The vacation is a dud, as Bangkok was, and you get busy planning your next adventure in a few months.

The quantity of trips can also impact your vacation mindset. Because Tom knows it’s his one travel opportunity of the year, he’s under a good deal of self-imposed pressure to make the most of it. Maybe he’s tired after a morning sightseeing around Piccadilly Circus, but to spend the afternoon relaxing in the hotel would be a waste of precious, limited vacation time. What was supposed to be a break from life’s demands can easily turn into an obligation of its own. It’s exhausting.

If you know you have more travel coming up soon, like Priya, you can take a more relaxed approach. You can be more charitable to yourself and any traveling companions once you stop feeling the need to always be going at full speed. Vacations become carefree adventures again.

The frequency of your trips even has an impact on your well-being after you’ve returned home. When Tom got back from London, with no money left in his flight budget, he knew it’d be a year until his next vacation. A long, dreaded wait. In the meantime, there was little escape from the day-to-day drudgery.

For Priya, though, taking a trip every four months or so meant the vacation excitement cycle could begin as soon as she got back home. While Tom was pitying himself for how long it would be until his next trip, Priya was busy planning hers.